Phenazinium Salt-Catalyzed Aerobic Oxidative Amidation of Aromatic Aldehydes

被引:100
作者
Leow, Dasheng [1 ,2 ]
机构
[1] Inst Bioengn & Nanotechnol, Singapore 138669, Singapore
[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
AMIDE BOND FORMATION; LIGHT PHOTOREDOX CATALYSIS; 5-METHYLPHENAZINIUM SALTS; SUCCINIC DEHYDROGENASE; AQUEOUS-SOLUTION; AMINES; PHOTOCHEMISTRY; ESTERIFICATION; ALCOHOLS; PEPTIDE;
D O I
10.1021/ol5029354
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catalytic loading (1-2 mol %). The reaction proceeds at ambient temperature and uses air as the sole oxidant. The operationally easy procedure provides an economical, green, and mild alternative for the formation of amide bonds.
引用
收藏
页码:5812 / 5815
页数:4
相关论文
共 65 条
[1]   Developments in peptide and amide synthesis [J].
Albericio, F .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (03) :211-221
[2]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[3]   Photochemical Reactions as Key Steps in Natural Product Synthesis [J].
Bach, Thorsten ;
Hehn, Joerg P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1000-1045
[4]   N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].
Bode, Jeffrey W. ;
Sohn, Stephanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+
[5]  
Castanho M, 2011, PEPTIDE DRUG DISCOVERY AND DEVELOPMENT: TRANSLATIONAL RESEARCH IN ACADEMIA AND INDUSTRY, pXIII
[6]   PHOTOCHEMISTRY OF 5-METHYLPHENAZINIUM SALTS IN AQUEOUS-SOLUTION .2. OPTICAL FLASH-PHOTOLYSIS AND FLUORESCENCE RESULTS AND A PROPOSED MECHANISM [J].
CHEW, VSF ;
BOLTON, JR ;
BROWN, RG ;
PORTER, G .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (15) :1909-1916
[7]   PHOTOCHEMISTRY OF 5-METHYLPHENAZINIUM SALTS IN AQUEOUS-SOLUTION - PRODUCTS AND QUANTUM YIELD OF THE REACTION [J].
CHEW, VSF ;
BOLTON, JR .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (15) :1903-1908
[8]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[9]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[10]   Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis [J].
De Sarkar, Suman ;
Studer, Armido .
ORGANIC LETTERS, 2010, 12 (09) :1992-1995